X-ray diffraction and VT-NMR studies of (E)-3-(piperidinyl)-1-(2′-hydroxyphenyl)-prop-2-en-1-one

Seunghyun Choi, Yunhye Kim, Bernie Byeonghoon Park, Suzie Park, Jonghyun Park, Kiwon Ok, Jaehyung Koo, Yong Woo Jung, Young Ho Jeon, Eun Hee Lee, Ken S. Lee, Youngjoo Byun

Research output: Contribution to journalArticlepeer-review

Abstract

A series of 1-aryl-3-(cyclicamino)-prop-2-en-1-one analogs was synthesized from commercial acetophenones in 2 or 3 steps. Compound 6, (E)-3-(piperidinyl)-1-(2′-hydroxyphenyl)-prop-2-en-1-one, exhibited the unique shape and intensity of the Csp2NCH2peaks in the 1H and 13C NMR spectra. Variable temperature (VT) nuclear magnetic resonance (NMR) and X-ray diffraction (XRD) studies of 6 revealed that the piperidine ring has a lower energy barrier to rotation than the 5-membered pyrrolidine 9 due to the less effective π electron delocalization along the Csp2N bond.

Original languageEnglish (US)
Pages (from-to)600-605
Number of pages6
JournalJournal of Molecular Structure
Volume1076
DOIs
StatePublished - Nov 5 2014
Externally publishedYes

Keywords

  • Enaminones
  • Flexible rotation
  • VT-NMR
  • X-ray diffraction

ASJC Scopus subject areas

  • Spectroscopy
  • Analytical Chemistry
  • Inorganic Chemistry
  • Organic Chemistry

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